


“I Don’t Beg”

by lSuperDuperNaturall



Category: Supernatural
Genre: Alternate Universe - High School, Anal Sex, Bottom Jack Kline, Car Sex, Closeted Character, Closeted Sam Winchester, First Time, Jack kline - Freeform, M/M, Prostitute, Prostitute Jack Kline, Riding, Sam Winchester - Freeform, Slow Sex, Teen Jack Kline, Teen Sam, Teen Sam Winchester, Top Sam Winchester, car blowjobs
Language: English
Status: In-Progress
Published: 2018-04-05
Updated: 2018-04-05
Packaged: 2019-04-18 18:12:53
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,216
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14218872
Author URL: https://archiveofourown.org/users/lSuperDuperNaturall/pseuds/lSuperDuperNaturall
Summary: Closeted Sam seeks out Prostitue Jack





	“I Don’t Beg”

**Author's Note:**

> Thanks so much for all the comments and suggestions! They really helped!

"You can do this, Sam. You worked overtime for 2 months. You deserve this." he told himself sternly, before he drove into the alleyway, scrunching up his nose at the smell of sex and alcohol, lightly tinged with weed. He had to drive a damn town over, just to be extra sure that no one would recognize him.

This was _so_  not legal on so many levels. Sam wasn't even permitted to be driving after 11 pm, technically, so if he was pulled over, he was fucking _done_ for.

 

He rolled down the windows and looked out, ignoring the women in tight shirts with half their damn tits poking out altogether. If he was going to do this, it had to be perfect. Sam kept looking around looking for the perfect boy, suddenly, through all the smoke, almost like a fairytale, bright blue eyes found Sam in the dark, and his heart skipped a beat.

 

Jack shifted on his feet a little, his skinny jeans starting to get uncomfortable. It was a pretty average night, 3 of his regular clients had come by, none had fucked him, though. Just 2 quick, sloppy, blowjobs, and there was a weird guy with a making out kink or something, so he just used Jack against the wall and absolutely ravished his mouth for 20 minutes, but hey, Jack wasn't complaining.

 

His hardened cock was making a nice bulge in his skinny jeans, and he was getting some looks, but so far, no takers. He was damn near just closing up shop and going to his run-down apartment, just calling it a day when a car rolled up next to him, the window rolling down.

 

Now, Jack expected a 30-year-old man, at least. He was so popular because he reminded men of their youth, made them feel young again, he let them do what they hadn't got the chance to 15 years ago, but instead he saw a fresh-faced fucking.... kid. A year older than Jack, maybe.

 

"You lost?" Jack asked, smirking a little, noticing how nervous and surprised he looked, which Jack reveled in.

 

Making his voice gruff and face stoic, Sam shook his head.

 

"How much do you charge?" He asked, sitting up taller in his heat, surprised at how well he was faking confidence, but that fell apart when the guy sauntered over to his car. 

 

"I don't know," Jack said lightly, shrugging. "What do you want?" Sams' eyes dropped down to his lips, licking his own.

 

"Whats your name?" Sam asked, always a polite little boy.

 

"Jack." He purred, leaning forward, his head practically inside of Sams car. "And you?" He asked in a sultry whisper, which Sam immediately fell prey to.

 

"Sam." Jack gave him a once over.

 

"Well, Sam, how much do you have?" Jack wasn't used to dealing with guys his own age. He placed Sam at about 17 or 18, while Jack remained at a solid 16, his birthday next month. He hated what he did, but with a long-gone father and a mother stretched too damn thin across her 2 jobs, Jack was pulling the slack, cleaning, even teaching himself how to cook.

 

He brought money home, which usually paid that last bit of rent his mom just _didn’t_  have. His mom was grateful, didn't really ask any questions, and for that, Jack was mostly content. He shook himself out of it and looked over Sams car. Nice, a sleek white Jeep Wrangler, had to cost at least $33,500. Rich prick probably never had to worry about money in his life. The bright white, probably new, the color of the car matched Sams perfect teeth, and Jack had to shake himself a little, there was hatred boiling in him, fueled by jealousy and annoyance. He wasn't sure why he was so annoyed, but this.... Sam, or whatever his name was, just seemed like his life was perfect, and it was pissing Jack off.

 

"Uh, hello?" Sam awkwardly asked, noticing Jack was scowling at him.

 

Jack snapped out of it and looked at Sams outfit. Lettermen's jacket. Classic, Jack snorted. Probably the quarterback, too.

 

"Yeah, pretty boy? Don't worry, I'm not going anywhere." Jack purred, winking at Sam.

 

"You asked how much I have. Uhm, about 1,300. Figured that'd cover everything." Sams' voice was a little shaky as he pulled out his small wad of cash. "I read online you guys only take cash, so...." He said timidly.

Jacks eyes widened at the sight of all the money.

 

"Sold." He mumbled, walking around and slipping into the car. "You wanna do this in here or in a motel?"

Sam looked at him with wide eyes. "You'll do it?" He asked, still somewhat shocked.

 

"I just said I would, didn't I?" Jack looked at him with a raised eyebrow. "Now let's go, I haven't got all night."

Sam took in a sharp breath and nodded, driving away, following Jacks instructions until they got to an abandoned parking lot. The car ride had been mostly silent, giving Jack some time to think and figure out what kind of guy Sam was. He was nervous, so a first timer. His phone was face-up and on, so Jack figured he was usually a pretty good kid, wasn't hiding anything. This was probably the worst thing Sam would ever do. Sams phone did buzz once, he got a notification, and Jack could see his background was his prom pictures with his girlfriend.

"She's pretty." Jack dully commented while Sam parked. "Whats her name?" Jack smirked as Sam stiffened and grabbed his phone, shoving it in his pocket. "I can walk out of this car right now." Jack threatened, just to see how much Sam wanted this.

 

"Jess." Sams' voice was tight as his hands tightened on the steering wheel. Jack chuckled and looked at Sams tense figure.

 

"I'm not gonna fucking track her down, Sam. Calm down." Jack chuckled as Sam parked. "Backseat, now." And just like that, Jack went from a regular, 17-year-old kid, to a hooker, master of his craft. "I'm gonna make you fucking _beg._ " He said lowly, his voice sultry.

 

At that, Sams dick perked up, even more so, and he felt his mouth go dry.

 

"I don't beg." Sam snorted, clambering into the backseat, plopping himself down in the backseat, watching Jack climb over also and slip to his knees in front of Sam, who spread his legs wide, for Jack to crawl between.

"Why are you even here?" Jack looked up at Sam from on his knees, his blue eyes shining in the dark of Sams car.

 

"You're attractive..." Jack ran a hand up Sams clothed chest, feeling the other boy shudder under his touch.

 

"You don't need to come get some whore to _fuck._ " Jack practically sneered the word 'fuck', like it was an action full of violence and hatred, and that's probably what Jack was used to, being a prostitute and all.

 

"You could get any guy you wanted.." He whispered before his hand stopped at the 'W' on Sams letter jacket.

 

"Is this why, hmm?" He asked softly, almost as if he pitied Sam, which he kind of did. Most of his clients were closeted, that's why they just got anonymous hookers, someone who could fulfill their fantasies for a night before they went back to their girlfriends.

 

"Scared they'll bully you, Sam? Other guys on the football team?" Sam swallowed thickly. Of fucking _course_ that was why. He shifted a little, looking down at the kid who was a year younger than him, maybe more.

 

"Are you gonna suck my cock or not? I paid for the full package." Sam tried to make himself seem in control, demanding, but his voice was shaking, and his cock was making a bulge in his jeans.

 

Jack just chuckled and rolled his eyes. "I could kiss you and walk out of here, Sam. And you'd be fine with it" He whispered the last part, both of them knowing it was true. Sam's bottom lip just trembled slightly and he slumped back, still looking over Jacks features.

 

"Please.." he begged, his voice quiet and wavering, and it was the voice of a pleading man. Jack really did feel bad for Sam, the poor man was probably gonna marry his girlfriend and live a damn sad life.

 

"Sure, Sweetheart." He purred, reaching his hands forward to unzip Sams pants.

 

Sam almost opened his mouth to tell Jack not to call him that, but he kept it closed and just let himself enjoy what he had been lusting after for years, what he had saved up for damn near 2 months so he could afford.

Jack chuckled to himself and pulled the flaps of Sams jeans apart, biting his lip at the bulge in his black boxers. Okay.... so Sam was packing something... Jack licked his lips and pulled the stretchy elastic of Sams boxers to the side and his mouth watered a little at the sight of Sams nice, thick cock.

 

Sure, Jack was trying to act all in control and everything, but he felt as inexperienced as Sam did. Jack had never dealt with someone this attractive and close to his age and truth be told, he was getting kind of nervous.

 

"What, am I small?" Sam tried to joke, squirming around, nervous, his heart feeling like it was going to jump out of his damn chest.

 

Jack shook his head and licked his lips. "Not at all..." He whispered, leaning forward, taking a deep breath, his mother flashing through his mind for a quick second before he pushed her out of his mind and took Sams cock into his mouth, which already had pre-cum beaded at the tip, and Jack let out a soft little moan, his classic act, knowing it would drive guys crazy, and it sure worked on Sam, who bucked his hips up. "Easy there, tiger..." Jack purred, his words garbled around Sams thick cock in his mouth. Jack let his eyes flutter closed and he started bobbing his head, taking more of Sam into his mouth, loving how his jaw ached with the stretch.

 

"F-Fuck..." Sam gasped out, forcing himself to keep his hips down, so damn _scared_  that Jack would leave.

 

"Jack...." he begged, not even knowing what he wanted, just knowing he wanted more.

 

"I thought you paid for the full package?" Jack mocked, pulling off of Sams cock to speak.

 

"Please, just let me fuck you..." Sam begged, and Jack smirked, pulling off his shirt.

 

"Give me a sec, Sammy." He grinned. "Need to undo my pants." Jack was having fun with this kid. With a few grunts, Jack managed to get his shoes and pants off, he didn't bother with boxers, while still seated on the floor of Sams car. He crawled into Sams lap, naked, save for a devilish smirk and pressed their lips together, feeling the big jock melt under him and let out a strangled whimper into Jacks mouth, which he stored for later. Hey, Jack needed to get off, too. jack reached under Sams shirt and ran his hands over Sams abs, feeling Sams shaky hands come up and start gently groping his ass.

 

"'M not gonna break, Sammy," Jack whispered against Sams lips, that were barely moving, Sam was so overwhelmed and overtaken with shock that he could barely do what he wanted. At that, Sams grip got a little firmer, a little more confident as he ran his hands all over Jacks lithe body, pulling him closer until their dicks were pressed together, between Sams shirt and Jack's bare abdomen.

 

"Are you gonna...?" Sam couldn't even finish his sentence as he blushed, embarrassed.

 

 

"Am I gonna what?" Jack wanted to hear him _say_ the damn words, admit to Jack and himself what he really wanted.

 

"Ride me?" Sam said after a minute of biting his lip and looking at Jack with wide eyes.

 

"Since you asked so nicely..." Jack purred into his ear and kissed Sams lips for a final time before he pulled away and lifted his body, positioning his hole, already stretched and lubed over Sams dick before he froze. Fuck! He couldn't believe he had almost forgotten. He usually never forgot.

 

"Something wrong?" Sam asked, looking at Jacks dick, almost as if he were asking it the question. Jack nodded.

 

"Condom?" He didn't wanna use one, he really didn't, but he had to.

 

"I’m clean." Sam was quick to say, looking at Jack with wide eyes.

 

"Mhm, yeah," Jack said sarcastically, and Sam reached forward, a hand wrapped around Jacks' waist so he wouldn't fall, and got out some papers from the glove compartment.

 

"I got myself tested yesterday...." He handed the papers to Jack who read them over and grinned.

 

"Well, I'm clean since I always use a condom. So in a way, you're my first." He winked at Sam, who moaned softly and he reached down, grabbing Sams hard dick and pressing it against his already slick and loose hole. Jack always prepped himself at home.

 

"Fuck..." Sam breathed out and he threw his head back and stared at the ceiling, waiting for Jack.

 

"Now?" Jack teased, and Sam nodded.

 

"Yeah, now, please." He begged, and Jack started to sink down on Sams cock, the sensations rolling through Sam and making him snap forward, wrapping his arms around Jack, breathing heavily, their bodies pressed together.

 

 

"Jack..." He whispered out, his voice broken, almost as if he had the large cock up his ass.

 

"Please.." Funny, Sam seemed to be saying that a lot. Sam was shaking lightly, his arms wrapped tight around Jacks slim torso.

 

Jack shifted a little, his hole stretched tight around Sams cock, before he took a deep breath and started rocking back and forth on Sam, making Sam moan out loudly, his nails digging into Jacks back.

 

"H-How can you do this every day? Isn't it o-overwhelming?" Sam gasped out, the waves of pleasure rolling through his body.

 

"Some of us aren't fucking virgins, Sammy." Jack whispered into Sams' ear, lightly biting the shell.

 

Sam shuddered lightly at that and his nails dug into Jacks back, making Jack jump a little and start bouncing on Sam's thick cock again, his rim stretching around it, and Sam seemed to be so damn far gone.

 

"You gonna leave her?" Jack moaned out, slowly bouncing on Sams cock.

 

"Who?" Sam was confused, and for a second he almost forgets all of his wet dreams were coming true.

 

"Your girlfriend." Jack breathed out, closing his eyes, his rim stretched tight around Sams thick cock.

 

Sam stilled and looked into Jacks eyes, still not understanding.

 

"For me, Sammy..." Jack purred, his blue eyes meeting Sams'. "Would you leave her for me?"

 

And at that, Sam started nodding. "Yeah, Jack. I'd leave her for you in a heartbeat, fuckin marry you if you'd let me." Jack smirked, clenching around Sam again. He fucking _loved_ this, it made him feel amazing. He loved the fact that he had straight men lusting after him. He knew it was just their dick talking, but he relished in the fact that if Sam was given the opportunity, he'd leave his pretty blonde girlfriend for Jack.

 

"I'll leave her for you, Jack..." Sam kept mumbling, his arms wrapped tight around Jack, breathing heavily into Jacks smooth, bare neck.

 

Jack smirked and ran his hands through Sams long hair. "Good boy..." he purred, clenching around Sams thick cock, and to be honest Jack felt like he was damn near cumming, his cock was rubbing Sams Letterman's Jacket so fucking deliciously, the felt was sending Jack over the edge. Usually, Jack didn't cum, but there was something... different about Sam. Jack quickly shook that thought away and started bouncing again, just trying to get Sam to cum so he could cum and go drink and forget about everything.

"F-Fuck, Jack, can I cum in you?" Sam sounded like he was begging, which he kind of was as Jack sped up the pace, just 2 teenagers fucking in a car.

 

"Yeah, Sammy you can..... but I want to cum first." Jack had never made that request, and he wouldn't have been surprised if Sam ignored him, but Sam just nodded and kept kissing Jacks neck.

 

"I want you to feel good, too..." Sam murmured into Jacks' neck as he reached down and took Jacks cock in his hand and started pumping at the same pace Jack was going, which was pretty slow. Jack had never had anyone cum while he was going this slow, but it was Sams first time. Put away the damn whips and chains. Jack was so caught up in his own thoughts and just repeating the process of up and down and up and down on Sams cock that his own enjoyment didn't even catch up to him until he felt a surge of pleasure and he arched his back, letting out a wail as he came all over Sams jacket, getting splurts if white cum against the red and blue felt, making Jack smirk in satisfaction, his chest heaving a little with pleasure. He then remembered that Sam still hadn't cum and he sped up the pace, a little oversensitive, but he wanted to give Sam an orgasm to remember, so he leaned forward and trapped Sams lips in a deep kiss, the very definition of 'sucking face' as he sped up a little.

 

"Jagh~" Sam tried to moan while kissing Jack at the same time, and it wasn't long until Jack felt Sams nails raking down his back and he felt Sams cock twitch almost violently in him.

 

One more fucking clench of his hole and Sam was cumming deep inside the younger boy, and Jack pulled away from the kiss, throwing his head back as his and Sams moan filled the car the stench of sex strong in the air. After a minute, they were both panting and Jack looked at Sam and winked, feeling a little... frisky.

Jack grinned and leaned forward, kissing Sam, their tongues dancing together. Of course, Jack wanted this to be like some fairy tale, where Sam would break up with his girlfriend and run away with Jack or some shit, but that just wasn't gonna happen. With a heavy heart, Jack put on his clothes and climbed into the front seat again with Sam, the wad of cash in Jack's pocket as they drove back to the alleyway for Sam to drop Jack off. Sam seemed kind of reluctant, but he drove back to the spot he first picked up Jack and stopped, looking at Jack with longing puppy eyes, and Jack had to quickly get out of there before he did something stupid. Sam gave him a final look before he drove away, the white vehicle disappearing into the night.

 

"I love you," Jack whispered into the cool night air, condensation floating away from his lips into the cool night air.

 

And who knows?

 

Maybe that little puff of air followed Sam home.

 

At that thought, Jack chuckled to himself a little and looked down, kicking a small rock and shaking his head. God, he was cheesy. Jack grinned to himself and started walking home.

 

 

 

 

**Author's Note:**

> Smash that mf like button
> 
> Also leave comments plz


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